3695-36-1

Usage

Physical state

Liquid organic compound

Uses

Flavor and fragrance additive in consumer products

Scent

Pleasant, sweet, and fruity

Natural sources

Found in onion and garlic, contributing to their characteristic aroma

Industrial application

Precursor in the production of other organic compounds

Role in chemistry

Acts as a reagent in chemical reactions

Safety concerns

Volatility and flammability

Storage and handling

Should be stored in a well-ventilated area and handled with care to prevent potential hazards

InChI:InChI=1/C9H12S/c1-3-10-9-7-5-4-6-8(9)2/h4-7H,3H2,1-2H3

Upstream product

• 14092-00-3 methyl o-tolyl sulfide 
• 98-88-4 benzoyl chloride 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 615-37-2 ortho-methylphenyl iodide 
• 93-89-0 benzoic acid ethyl ester 
• 4032-80-8 bis(2-methylphenyl)disulfide 
• 20035-08-9 sodium ethanesulfinate 
• 100-68-5 methyl-phenyl-thioether 
• 19614-16-5 2-bromo-1-(methylsulfanyl)benzene 
• 75-03-6 ethyl iodide 
• 74-96-4 ethyl bromide 
• 137-06-4 2-thiocresol 
• 4646-69-9 benzocyclopropene 

Downstream Products

• 91952-80-6 N-(4-Ethylmercapto-3-methyl-benzyl)-propylamin 
• 97556-11-1 <4-Aethylmercapto-3-methyl-benzyl>--sulfid 
• 92854-94-9 <4-Aethylmercapto-3-methyl-benzyl>--aether 
• 67272-96-2 3-Methyl-4-ethylmercapto-benzylchlorid 
• 74-85-1 ethene 
• 13963-35-4 2-(phenylthio)toluene 

Relevant academic research and scientific papers

Electrochemistry Enabled Nickel-Catalyzed Selective C?S Bond Coupling Reaction

This work describes an electrochemical enabled nickel-catalyzed chemoselective C?S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C?S bond coupling has demonstrated excellent redox activity, scalability and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.

Production of Alkyl Aryl Sulfides from Aromatic Disulfides and Alkyl Carboxylates via a Disilathiane–Disulfide Interchange Reaction

The results of this study show that disilathiane is an effective mediator in the synthesis of alkyl aryl sulfides with disulfides and alkyl carboxylates. Mechanistic studies suggest that disilathiane promotes cleavage of the sulfur–sulfur bond of disulfides to generate thiosilane as a key intermediate. Diselenides were also applicable to this transformation to produce the corresponding selenides.

Copper-Catalyzed Three-Component Coupling Reaction of Aryl Iodides, a Disilathiane, and Alkyl Benzoates Leading to a One-Pot Synthesis of Alkyl Aryl Sulfides

A copper-catalyzed three-component coupling reaction of aryl iodides, hexamethyldisilathiane and alkyl benzoates leading to alkyl aryl sulfides has been demonstrated. A disilathiane acted as both a sulfur source and a promoter of the sulfidation, and the alkyl moiety of the alkyl benzoate was effectively introduced on one side of the sulfide. Moreover, we found that the protocol can be expanded to the preparation of ethyl phenyl selenide with diphenyl diselenide.

Metallation reactions. Part 35: A change of the regiochemistry in the metallation of (alkylthio)arenes

The metallation reaction of bromo(alkylthio)benzenes is described. The results show the complementarity of these reactions with the metal-hydrogen exchange reaction. In fact, monometallation of bromo(methylthio)benzenes afforded products substituted in para or meta or ortho to the thioethereal function while bimetallation led to αS,para, αS,meta and αS,ortho disubstituted products. Analogously, the monometallation of 4-bromo-(isopropylthio)benzene afforded para-monosubstituted and ortho,para-disubstituted products.

Studies in the Cycloproparene Series: Reactions with Radicals

The behaviour of 1H-cyclopropabenzene (1) and 1H-cyclopropanaphthalene (23) towards a variety of radicals results in opening of the three-membered ring to give ortho-substituted benzyl and 2-methylnaphthalene derivatives, e.g. (13) and (28), respectively.Ring expansion into the cycloheptatriene manifold by way of addition to the bridge bond and norcaradiene formation have not been observed.Analogous reactions with the methylidenecyclopropanaphthalenes (33) and (34) lead to much decomposition, and provide little evidence for the C 1 cycloproparenyl radicals (35) and (36).

Metallation reactions. XXI. Metallation of alkyl (alkylthio) benzenes by superbases versus organolithium compounds

The metallation regiochemistry of alkyl(alkylthio)benzenes with butyllithium or with the superbasic mixture of butyllithium with potassium tert-butoxide is described. The reaction pattern depends on the substrate and the reagent. Butyllithium monometallates the thiomethylic carbon of methyl (methylthio) benzenes and bimetallates the thiomethylic and the annular carbon ortho to the thioethereal group. With superbases the metallation occurs at the thiomethylic and methylic carbon. Metallation with butyllithium of the higher homologs substitutes exclusively the hydrogen ortho to the thioalkylic group, while the superbases attack also the carbon atom alpha to the thioalkyl substituent.

Metallation Reactions. XVIII. Regioselective metallation of (alkylthio)benzenes by superbases

(Alkylthio)benzenes were monometallated at the alpha position by a stoichiometric mixture of butyllithium and potassium t-butoxide and bimetallated at both the alpha and the ortho positions by two equivalents of the same reagent.

METALATION REACTIONS. XIV. REGIOSPECIFIC PREPARATION OF POLYSUBSTITUTED BENZENES VIA MONO- OR DI-LITHIATION REACTIONS OF AROMATIC THIOETHERS

The preparation of polyfunctionalized aromatic thioethers either by one-step dilithiation or by two successive one-flask monometalation reactions is described.By acting on 1 two equal or different electrophiles one on the thiomethyl group and one in the ortho-position with respect to it are introduced; by acting on 11 and on 35 the substitution involves the thiomethyl carbon atom and that in the ortho-position with respect to the alkoxy group.In the case of the homologeous isopropylthio (23) the substitution involves the two aryl carbon atoms in the ortho-position to both functions.In the case of the p-disubstituted isomers (49, 59) analogous behaviour to ortho isomers in one-step metalation reaction is observed, while the two hydrogen atoms in the ortho-positions to the methoxy group are substituted when two successive monometalations are employed.The metalation of 40 results low selective.The behaviour of 79 and 93 is analogous to 1, while 72, 88 and 96 undergo only one-step monometalation reactions.

Metalation reactions XIII. The reactions of electrophiles with the dilithiated species 1-(α-lithiomethyl)-2-benzene

Direct dimetalation of 1-methyl-2-(methylthio)benzene (1) gives the dilithiated species (2) in good yield, which can be used to introduce substituents into the thiomethyl and methyl groups.Species 2 can react also with a variety of dichlorosilanes and dichlorostannanes, and with sulphur chloride, to yield derivatives of 1,3-benzothiasilin, 1,3-benzothiastannin and 1,3-benzodithiin respectively.Reaction of 2 with tetrachlorosilane yields a spirocyclic silicon compound, while reaction with benzoyl chloride yields a derivative of 1-benzothiopyran.

METALATION REACTIONS. IX. DILITHIATION OF AROMATIC THIOETHERS

Direct dimetalation of aromatic thioethers gives with good yield the dilithiated species 3, 4, 17, 18, 25, 26.The first four species allowed the simultaneous introduction of an electrophile in the thiomethyl group and in the ring, while the last two species undergo disubstitution in the ring.